Sodium Hydroxide → HCID 42641719, compound

HRID 1909611Notes

Reaction equation

C[O:2][C:3](=[O:27])[CH2:4][CH2:5][CH2:6][N:7]1[CH2:11][CH2:10][CH2:9][C@H:8]1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:16][CH:15]=1.[OH-].[Na+]>CO.O>[CH2:20]([C:17]1[CH:18]=[CH:19][C:14]([O:13][CH2:12][C@@H:8]2[CH2:9][CH2:10][CH2:11][N:7]2[CH2:6][CH2:5][CH2:4][C:3]([OH:27])=[O:2])=[CH:15][CH:16]=1)[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1

Participants

Conditions

Temperature: 50 °C

Procedure

To a solution of the product from step 1 (0.13 g, 0.35 mmol) was added 2N NaOH (0.29 mL, 0.58 mmol) and 80% MeOH/H2O (4 mL). The resulting slurry was stirred at 50° C. for 67 h. The solvent was removed under reduced pressure and water was added to the residue. The pH was adjusted to 4 using 1 N HCl solution. The crude product was extracted with ethyl acetate. The combined organic layers were washed with water, washed with brine, dried over anhydrous Na2SO4 and concentrated in vacuo to afford the title compound (0.09 g, 77%) as a yellow semi-solid. 1H NMR (400 MHz, CDCl3); δ 1.96-2.26 (m, 6H), 2.41 (t, J=6.6 Hz, 2H), 3.02 (m, 2H), 3.47 (m, 1H), 3.67 (m, 2H), 3.89 (s, 2H), 3.85 (dd, J1=4.0 Hz, J2=10.8 Hz, 1H), 4.50 (m, 1H), 6.84 (d, J=8.8 Hz, 2H), 7.09-7.19 (m, 5H), 7.25-7.28 (m, 2H); MS (m/z) 352.4 (M−1); LC (97.6%); HPLC (96.6%).

Workup

customThe solvent was removed under reduced pressure and water
additionwas added to the residue
extractionThe crude product was extracted with ethyl acetate
washThe combined organic layers were washed with water
washwashed with brine
dry with materialdried over anhydrous Na2SO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-988fe6b4f8a14d32a183b67647592f1a
Source dataset: uspto-grants-2013_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08598359B2

Reaction notes

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